


With Friends Like His...

by HeroFizzer



Series: PaytreeOn Prompts [7]
Category: Highschool DxD (Anime)
Genre: Creampie, Cuckolding, F/M, Gangbang, Multi, Oral, Threesome - F/M/M, ntr
Language: English
Status: Completed
Published: 2020-04-05
Updated: 2020-04-05
Packaged: 2021-03-01 01:22:09
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,990
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23486743
Author URL: https://archiveofourown.org/users/HeroFizzer/pseuds/HeroFizzer
Summary: Issei finally goes through with his end of an old promise to his friends, letting them have some time with Rias. The Gremory girl will only do it, however, on the condition that her boyfriend doesn't get to see it.
Series: PaytreeOn Prompts [7]
Series URL: https://archiveofourown.org/series/1552588
Comments: 1
Kudos: 14





	With Friends Like His...

Issei was covered in sweat as he stared at Rias, who sat behind the desk she used as president of the Occult Research Club, held her eyes shut while her shoulders rested atop it. He knew this would be trouble for him, but he at leadt expected something, ANYTHING, from the crimson haired devil. The silence was the worst thing he could possibly experience, as it made the inevitable lecture he would receive all the worse when it finally came.

After what must have been a lifetime to the Breast Dragon Emperor, Rias finally lifted her head, inhaling through her nostrils before opening her eyes up. The deathly glare he received from his girlfriend was a telling sign of just how in deep he was. "Let me get this straight," Rias said, her voice cold and flat, "you and your friends made a promise with one another that when one of you finally obtained a girlfriend for yourself, you would allow the others to have a turn with her?"

"Yup! Yeah, that's...that's the gist of it, all right!" Issei said, smiling nervously despite the redhead's gaze burning a hole through his chest. "I mean now that I actually HAVE a girlfriend the whole thing feels really stupid, you know? I mean I couldn't have known how it felt once the time came about-"

Issei jumped back after Rias stood up, slamming her hands atop the desk. "So instead of trying to break off the deal, you INSISTED that it would happen? And now here you are making an attempt to go through with your pact?!"

"Rias, please, they kept nagging me about it!" Issei shouted, getting on his knees before the club president. "I tried to blow it off for as long as I could but they wouldn't listen to reason!"

Rias remained with her eyes on her boyfriend, watching him grovel for forgiveness. True, she could see his point; there was no certain way he could have seen them getting in so deep with one another, especially now that he was part devil. However, it would have been a good idea for him to address this from the start so she could handle it, rather than waiting until after that war stuff happened.

"Issei, I've long since accepted the fact you can be such a hound dog," Rias stated, "but as my boyfriend you really should be telling me these sort of things up front."

"I'm sorry..." Issei whimpered, lifting his head up to face the devil. "I really dropped the ball here, huh?"

"Of COURSE you did!" Rias barked. "Don't think that I'll be able to forgive you so easily, Issei. Just because you're sorry that doesn't mean everything can immediately be fixed!"

The Breast Dragon Emperor nodded solemnly, unable to say much else in his case. He screwed up, and he knew it all too well. "So, what do we do then?"

"I could have their memory erased over the pact," she said, approaching the window that oversaw the street by their club building, "however, we're a little too late to do that."

Issei rushed to the window, seeing his pals yucking it up as they made their way to the building. He had forgotten that he told them to meet him there after class, as he was originally looking to convince Rias to go along with it. "Aw crap..." Issei groaned.

"So I'm going to go ahead and follow up on your promise." Rias said, brushing her long crimson hair behind her ear. "However, there's one condition I want from you."

"Anything." said Issei, aware he was beyond helpless.

"You can't watch."

"AW COME ON!" shrieked Issei. "That was supposed to be the whole POINT of this!"

Turning her nose up at him, Rias said, "Then that seems as fitting a punishment as you deserve. Perhaps next time you'll learn to discuss these things with me rather than keep it some sort of dirty little secret until peer pressure takes over."

"Yes, Rias..."

"Now go ahead and welcome them inside. I'm going to get a bit more comfortable in the meantime."

Issei hung his head as he left the room, unable to watch Rias remove her blouse and let her huge breasts hang out. His friends were about to have the ride of a lifetime, and all he could do was miss out on the fun.

##

"Yo Issei! About time, bro, where were you?!" asked Matsuda as he and Motohama stepped inside.

"Oh you know, helping Rias get ready for you." Issei replied, trying to keep a smile on for his friends. He was still annoyed that he would be missing out on the fun, but the most he could do was be thrilled for his friends that they'd be losing their virginities. Even if he had yet to do so himself.

"This is gonna be the best afternoon ever, man!" Motohama shouted as he punched the air, following behind Issei up the stairs. "Man, I knew this day'd come when we got to do this, but who knew you'd land Rias Gremory as your catch?!"

"For real, man!" laughed Matsuda, wearing a huge grin on his lips. "I'm so excited I can't hold my boner back!"

"Dude, TMI." whispered Motohama.

They finally made it to the president's room, where Issei took a deep sigh as he stood outside the doors. He wasn't quite prepared for this, feeling intensely jealous for his friends, but he supposed there was a bright side to this agreement; he wouldn't be able to see the good time his friends were having with Rias.

...that just made him even sadder.

He eventually opened the doors, letting Matsuda and Motohama stare in the office, where Rias was sitting on her desk in nothing more than a towel, a seductive expression in her eyes. Issei knew they were for his friends, but it was still amazing to him how quickly Rias could flip the switch that.

"Hello, boys," Rias said, batting her eyelashes at her boyfriend's friends, "are you finally here to claim your end of the bargain? You've been waiting patiently for this moment, I'm sure." Their jaws dropped at the immediate sight of the most attractive girl at school, who was already naked for them. Issei looked on in disgust, seeing his girlfriend pulling back no punches to make him feel even dumber for his choices.

When their minds had refreshed from the crash of reality they were given, Matsuda and Motohama gathered around the crimson haired princess, still unaware of her true devilish nature. But they liked what they saw as her purple towel slipped of its own will, showing off the areolas and nipples that were hidden underneath. Rias chuckled to herself, seeing the astonished eyes of Issei's friends, as if they had never seen a woman's breasts before. “I hope you don't mind my appearance,” she said, lifting her head to stare at her beau, “I just slipped out of the shower.”

With a nudge in his direction, Issei took the hint. He wasn't needed in this scenario, and could only hear the pleasant moans of ecstasy that would come from Rias's office. He hated it, but what else could he really do?

“Hm? Don't be shy, boys.” Rias said in a seductive tone, jutting her chest out for Matsuda and Motohama. “Give them a little kiss.” The pair of friends did just that, locking lips with the devil's orbs while lowering their heads to meet with them. Rias moaned, sucking on her lower lip while the sensitive nips were sucked on by her boyfriend's acquaintances. 

Rias moaned as she felt their teeth pushing into her nipples, grinding away on them as if they were trying to break her in. Motohama couldn't help but suction his whole mouth to Gremory's breast, just for the sake of pulling it off her chest, then letting go as it dropped back down with a hard slap. Rias moaned as Matsuda gripped the breast he suckled on tightly, giving it a squeeze, as though he were going to pop it like a balloon. Although that wouldn't be possible, the crimson haired devil never saw anyone try to fondle her in such a fashion.

When they had their share of titty touching, Rias dropped to her knees, letting the towel fully drop down from her naked body. “Okay, boys,” said the devil in a seductive tone, “let's see what you have to offer.”

In a flash, Issei's friends dropped their pants without missing a beat, leading the devil to wonder how they did that without even loosening their belts. Their peckers were huge, larger than what she had seen her boyfriend sporting. Matsuda was obviously lengthier compared to his glasses wearing friend, being nine inches compared to eight, but Motohama had the thickness. Both were leaking precum rather fierce, drooling down to the knees. Rias was quick to lap up the clear liquid, bringing her open mouth up to their tips as it gathered onto her tongue. Her lips then went right to Matsuda, clearly showing favoritism in length over girth, while she wrapped her hand around Motohama's member.

“Oh, fuck, her lips are so soft!” Matsuda sighed, growing relax over the president's oral service.

“Man, you should feel this massage on my dick...” Motohama said with a whimper of joy. “She really knows what she's doing.”

Rias enjoyed the praise, but she had little experience in this matter. She only imitated what she had seen the JAV performers in Issei's tapes do, though by the sounds of their positivity she was doing well enough for a first time. Her lips moved down Matsuda's dick, slurping up any saliva that she left behind, while Motohama quivered from the gentle touch that his friend's belle provided his rod. Her slender fingers managed to fit around his girth with ease, something he thought no woman could actually do.

When Matsuda was coated in her spit, Rias moved her lips over to Motohama, making sure he was given a good tongue twister as well. The bald friend wrapped her fingers around his dick next, lathering the saliva into his skin just to smooth it out. She was particularly fond of the friend with glasses and his precum, as it seemed nonstop in how it poured from the urethra, like a faucet desperate in need of fixing. It seemed to her as though he was desperate for release.

Matsuda was next to quiver from the hand job Rias gave him, drooling from the mouth as her thumb played with his crown. The fingernail was especially eager to tease the slit, having some thoughts of going as deep as it would allow. But with the small size, she could only get so far, though seeing how Matsuda trembled and sighed with a quaking voice, that was still good enough for his attention.

For her own entertainment, Rias decided to bring the tips of their dicks together, seeing the embarrassed expressions the two dudebros had, as if this was the gayest thing they had ever done. Rias found it cute that boys would get so nervous interacting with one another on such a sexual level, and yet she could think of a few times where her nipples have pressed into those of another woman. Their embarrassment was soon forgotten, as the crimson haired devil covered their tips with her lips, engulfing as much as she could before her tongue played around with them.

Matsuda and Motohama took deep breaths through their nostrils, holding themselves together and avoid releasing their seed on one another. The way Rias was working on their cocks was more intense than they could ever fap for themselves, as if she understood how she would have wanted to experience the pleasure of a woman's touch. But they couldn't find themselves willing to cum in the president mouth or even on her face.

As she flicked heavily at the tips, Rias chuckled, seeing the expressions on their faces. They were just like her boyfriend, trying to hold back for the sake of their own release. Though she could very easily make them cum now, she was far more interested in making Issei upset over not being able to see all this action. When she removed her lips from their dicks, the devil batted her eyes before asking, “Say boys, how badly do you want to fill my holes?”

She stood up, ignoring their dropped jaws as she walked over to the sofa, letting them get a glimpse of her ass as it swung behind her. The boys swore that one sway to the side was so hard that her ass cheek clapped into the other, but said nothing about it to their hostess. “Holy shit, man, I knew Rias had a banging ass but not like that.” whispered Matsuda.

“It's like something out of an anime...” Motohama said to himself.

As she laid on her back, Rias stared at the gawking male students and their throbbing boners, curling her finger in towards herself. “Come along, boys,” said the crimson haired devil with a wink, “I'm just aching to take those cocks.”

Rias began to rub her clit as she waited for the pair to get a move on, which she didn't have to do for very long. Matsuda and Motohama hurried over with mouths salivating, eager to shove their dicks inside their best friend's girl. The glasses wearing male couldn't help but shove his girth down Rias's throat from one end, while the student with the peach fuzz shoved his length into her snatch. Rias moaned loudly and wildly as their rods were injected inside her holes, loving how her canal and throat were being stretched out by their members.

As her mouth was being pumped into by Motohama, Rias hooked her arms around his legs, keeping him close to her while his dick forced her throat to push out for the sake of holding his thickness inside. Matsuda was ramming her crotch hard, holding her legs up high while her ankles rested on his shoulders. There was a trail of drool going down his chin that the club president couldn't see, but she imagined that he was growing more feral as he became aggressive with her body.

Both pairs of eyes were on Rias's breasts, which were jiggling hard atop her chest while they rammed their rods into her body. The balder of the two could see his dick was getting lubricated by Rias's fluids, which made it all the easier to slide inside her snatch and give it to her as hard as he could. Motohama only had the president's saliva to work off of, but he knew in a matter of time he was going to get his friend's beau adjusted to his thickness.

The moans the princess of ruin made was like music to her ears, whimpering as Motohama plugged up her mouth. She was getting wetter thanks to Matsuda's cock, her fluids spitting from her folds as he pulled away from every impactful jut. The veins on his cock were a clear sign that he was nearing release, and she could get the same feeling while wrapping her tongue around the glasses wearing student. Curious to see what they were capable of, the crimson haired devil let them do their worst.

It wouldn't be long after that the three came in unison, with Matsuda and Motohama holding their hips close to their respective holes while Rias's back arched into the air. The crimson haired girl cried out, her body quivering as she expelled her juices from her snatch just as Issei's bald friend splashed his milky jizz into her cervix, bouncing off before filling up her canal. The glasses wearing friend grinned as he growled, dumping his load inside of Rias's stomach. The president couldn't think of the last time she heard such satisfied moans of passion, but she enjoyed what she was hearing.

When things completed, Rias was able to stand up after the boys pulled their dicks from her mouth and muff, taking a seat on either side of her. “Not bad, boys.” said Rias, scooping some of Matsuda's cum from her snatch. It laid on her fingers for a bit before she put them in her mouth, swallowing it whole. “I'd say you did a better job than Issei ever could have, but I've yet to test his sexual stamina just yet.”

“No sweat...” Matusda panted. “Hey, maybe we can watch the action when you do it?”

Rias licked her lips, humming in thought on the request. “We'll see about it.” she replied, going for another mouthful of Matsuda's cum as it oozed from her snatch.

##

Later on, Issei sat on the sofa, gripping his pants as he heard the shower water running in Rias's shower. He could only imagine how much spunk his friends covered her in, much less filled her with, but it did annoy him that he couldn't witness it for himself.

“So I hope you learned your lesson, Issei.” said Rias from the shower, the running water coming to a halt.

“Yeah, never make a promise I don't intend to keep.” groaned Issei, looking up at the ceiling. “I hope you at least enjoyed yourself through the whole thing.”

Coming out of the shower, Rias had foregone a towel after drying herself off, walking to the sofa without anything on. She sat atop her boyfriend's lap, wrapping her arms around his neck. “That among others. But at least now you should understand the value of a relationship.”

“So...apology finally accepted?” Issei asked, trying to ignore the erection he was getting looking at his girlfriend's bare body.

“Apology accepted.” she replied, leaning in for a kiss.

Outside the room, Matsuda and Motohama fight over the singular keyhole to stare in from, trying to get a glimpse of the action they were bound to witness.

**Author's Note:**

> Thank you for reading!
> 
> If you'd like to follow for more content and community, as well as updates on my content, be sure to visit me here:  
> https://discord.gg/UEYU52  
> And here: https://twitter.com/HeroicFizzer


End file.
